Synthesis of 2,6-dihalogenated purine nucleosides by thermostable nucleoside phosphorylases

Advanced Synthesis and Catalysis

Volumn 357, Issue 6, 2015, Pages 1237-1244

  Zhou, Xinrui ^a   Szeker, Kathleen ^a   Jiao, Lin Yu ^b   Oestreich, Martin ^b   Mikhailopulo, Igor A ^c   Neubauer, Peter ^a  

^a Department of Bioprocess Engineering Institute of Biotechnology TechnischeUniversität Berlin   (Germany)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^c INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

biocatalysis; immobilization; nucleoside phosphorylases; purine nucleosides

Indexed keywords

EID: 84926631127     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400966     Document Type: Article

References (47)

1. P. Herdewijin, Modified Nucleosides: in Biochemistry Biotechnology and Medicine, Wiley-VCH, Weinheim, 2008
2. I. A. Mikhailopulo, A. I. Miroshnikov, Acta Naturae 2010, 2, 36-59
3. W. Sneader, Drug Discovery: A History, John Wiley & Sons, London, 2005.
4. T. Robak, P. Robak, Curr. Pharm. Des. 2012, 18, 3373-3388.
5. I. Bellezza, A. Tucci, A. Minelli, Anticancer Agents Med. Chem. 2008, 8, 783-789
6. L. Bastin-Coyette, C. Smal, S. Cardoen, P. Saussoy, E. Van Den Neste, F. Bontemps, Biochem. Pharmacol. 2008, 75, 1451-1460.
7. P. L. Bonate, L. Arthaud, W. R. Cantrell Jr, K. Stephenson, J. A. Secrist III, S. Weitman, Nat. Rev. Drug Discovery 2006, 5, 855-863.
8. J. A. Montgomery, K. Hewson, J. Med. Chem. 1969, 12, 498-504.
9. J. A. Montgomery, K. Hewson, J. Am. Chem. Soc. 1957, 79, 4559.
10. H. Wallen, J. A. Thompson, J. Z. Reilly, R. M. Rodmyre, J. Cao, C. Yee, PLoS One 2009, 4, e 4749.
11. S. G. McKenzie, R. Frew, H. P. Bar, Eur. J. Pharmacol. 1977, 41, 183-192.
12. G. M. Blackburn, M. J. Gait, D. Loakes, D. M. Williams, Nucleic Acids in Chemistry and Biology, 3 rd edn., Royal Society of Chemistry, Cambridge, 2006.
13. H. Vorbrüggen, C. Ruh-Pohlenz, in: Organic Reactions, John Wiley & Sons, Inc., New York, 2004
14. J. K. Watts, M. J. Damha, Can. J. Chem. 2008, 86, 641-656.
15. K. A. Watanabe, S. E. Patterson, in: Frontiers in Nucleosides and Nucleic Acids, (Eds.:, R. F. Schinazi, D. C. Liotta,), IHL Press, Tucker, GA 2005, pp 3-56
16. K. W. Pankiewicz, Carbohydr. Res. 2000, 327, 87-105.
17. B. G. Anderson, W. E. Bauta, J. W. R. Cantrell, T. Engles, D. P. Lovett, Org. Process Res. Dev. 2008, 12, 1229-1237
18. Y. Cen, A. A. Sauve, Nucleos. Nucleot. Nucl. 2010, 29, 113-122
19. T. Tennilä, E. Azhayeva, J. Vepsäläinen, R. Laatikainen, A. Azhayev, I. A. Mikhailopulo, Nucleos. Nucleot. Nucl. 2000, 19, 1861-1884.
20. I. A. Mikhailopulo, Curr. Org. Chem. 2007, 11, 317-335.
21. I. A. Mikhailopulo, A. I. Miroshnikov, Mendeleev Commun. 2011, 21, 57-68.
22. I. A. Mikhailopulo, A. I. Zinchenko, Z. Kazimierczuk, V. N. Barai, S. B. Bokut, E. N. Kalinichenko, Nucleos. Nucleot. 1993, 12, 417-422
23. V. N. Barai, A. I. Zinchenko, L. A. Eroshevskaya, E. N. Kalinichenko, T. I. Kulak, I. A. Mikhailopulo, Helv. Chim. Acta 2002, 85, 1901-1908
24. H. Komatsu, T. Araki, Nucleos. Nucleot. Nucl. 2005, 24, 1127-1130
25. G. Zuffi, S. Monciardini, (Explora Laboratories SA, Switzerland), European Patent EP1932918 A1, 2008
26. T. A. Krenitsky, G. B. Elion, J. E. Rideout, (The Wellcome Foundation Limited), European Patent EP0002192 B1, 1981
27. J. V. Tuttle, M. Tisdale, T. A. Krenitsky, J. Med. Chem. 1993, 36, 119-125.
28. S. Taran, K. Verevkina, S. Feofanov, A. Miroshnikov, Russ. J. Bioorg. Chem. 2009, 35, 739-745.
29. R. M. Arevalo, V. M. D. Thomas, C. L. Gõmez, M. P. Gilabert, C. E. Company, J. C. Boliart, (Institut Univ. de Ciència i Tecnologia), European Patent EP 2338985 A1, 2011.
30. T. A. Krenitsky, G. W. Koszalka, J. V. Tuttle, Biochemistry 1981, 20, 3615-3621.
31. D. Ubiali, C. D. Serra, I. Serra, C. F. Morelli, M. Terreni, A. M. Albertini, P. Manitto, G. Speranza, Adv. Synth. Catal. 2012, 354, 96-104.
32. D. F. Visser, F. Hennessy, J. Rashamuse, B. Pletschke, D. Brady, J. Mol. Catal. B: Enzym. 2011, 68, 279-285
33. D. V. Chebotaev, L. B. Gul′ko, V. P. Veiko, Russ. J. Bioorg. Chem. 2001, 27, 160-166.
34. R. Aono, K. Aibe, A. Inoue, K. Horikoshi, Agr. Biol. Chem. Tokyo. 1991, 55, 1935-1938.
35. C. Mateo, J. M. Palomo, G. Fernandez-Lorente, J. M. Guisan, R. Fernandez-Lafuente, Enzyme Microb. Technol. 2007, 40, 1451-1463.
36. B. Bertoša, G. Mikleuševic, B. Wielgus-Kutrowska, M. Narczyk, M. Hajnic, I. Leščic Ašler, S. Tomic, M. Luic, A. Bzowska, FEBS J. 2014, 281, 1860-1871
37. M. J. Pugmire, S. E. Ealick, Biochem. J. 2002, 361, 1-25.
38. I. Serra, D. Ubiali, J. Piškur, S. Christoffersen, E. S. Lewkowicz, A. M. Iribarren, A. M. Albertini, M. Terreni, ChemPlusChem 2013, 78, 157-165
39. I. Serra, T. Bavaro, D. A. Cecchini, S. Daly, A. M. Albertini, M. Terreni, D. Ubiali, J. Mol. Catal. B: Enzym. 2013, 95, 16-22
40. I. Serra, C. D. Serra, S. Rocchietti, D. Ubiali, M. Terreni, Enzyme Microb. Technol. 2011, 49, 52-58
41. D. Ubiali, S. Rocchietti, F. Scaramozzino, M. Terreni, A. M. Albertini, R. Fernández-Lafuente, J. M. Guisán, M. Pregnolato, Adv. Synth. Catal. 2004, 346, 1361-1366.
42. D. Brady, J. Jordaan, Biotechnol. Lett. 2009, 31, 1639-1650.
43. X. Zhou, I. A. Mikhailopulo, M. N. Cruz Bournazou, P. Neubauer, J. Mol. Catal. B: Enzym. 2015, 115, 119-127.
44. X. Zhou, K. Szeker, B. Janocha, T. Böhme, D. Albrecht, I. A. Mikhailopulo, P. Neubauer, FEBS J. 2013, 280, 1475-1490
45. K. Szeker, X. Zhou, T. Schwab, A. Casanueva, D. Cowan, I. A. Mikhailopulo, P. Neubauer, J. Mol. Catal. B: Enzym. 2012, 84, 27-34.
46. A. I. Zinchenko, V. N. Barai, S. B. Bokut, E. I. Kvasyuk, I. A. Mikhailopulo, Appl. Microbiol. Biotechnol. 1990, 32, 658-661
47. V. B. Berzin, E. V. Dorofeeva, V. N. Leonov, A. I. Miroshnikov, Russ. J. Bioorg. Chem. 2009, 35, 193-196.